US5200494A - One-pack type epoxide composition - Google Patents
One-pack type epoxide composition Download PDFInfo
- Publication number
- US5200494A US5200494A US07/683,047 US68304791A US5200494A US 5200494 A US5200494 A US 5200494A US 68304791 A US68304791 A US 68304791A US 5200494 A US5200494 A US 5200494A
- Authority
- US
- United States
- Prior art keywords
- epoxide
- diisocyanate
- mole
- chemical equivalent
- molecule
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
Definitions
- the present invention relates to a one-pack type epoxide composition.
- Epoxides having more than one epoxy groups in their molecule when combined and mixed with various curing agents, may be cured at ambient temperature or elevated temperature. Since the cured epoxides have excellent adhesion to various materials, they have been used in variety of fields of application such as adhesives and coatings, and in injection, dipping, casting and potting.
- the present invention is to provide, in the fields relating to epoxides, epoxide compositions which can be easily handled and have excellent curing characteristics. More concretely, the present invention is to provide one-pack type heat curing epoxide compositions which have excellent storage stability and can be cured in a short period of time at relatively low temperature.
- epoxide compositions are of two-pack type, and they have to be used immediately after mixing an epoxide and a curing agent or a curing accelerator.
- two-pack type epoxide compositions may be cured at room temperature or at low temperature, they have to be precisely weighed and mixed just prior to use. When wrong amounts are weighed relative to the correct amounts of the epoxide and the curing agent, or subsequent mixing is not sufficient even if correct amounts are weighed, there is a problem that the performance of the cured material is insufficient.
- limited pot life of conventional two-pack type epoxide compositions makes their adaptability to automated machines difficult. Thus, it is desired to produce one-pack type heat curing epoxide compositions to eliminate these drawbacks.
- One-pack type heat curing epoxide compositions need a latent-type curing agent which has a property of not reacting with an epoxide at room temperature but starting reaction to cure upon heating.
- Some latent-type curing agents have been proposed so far, and typically, there may be mentioned dicyandiamide, dibasic acid dihydrazides, boron trifluoride amine complex salts, guanamines, melamine and imidazoles.
- dicyandiamide, dibasic acid dihydrazides typically, there may be mentioned dicyandiamide, dibasic acid dihydrazides, boron trifluoride amine complex salts, guanamines, melamine and imidazoles.
- mixtures of dicyandiamide, melamine or a guanamine with an epoxide are excellent in storage stability, they have a drawback of necessitating a curing condition at high temperature above 150 ° C. for a long
- Japanese Unexamined Patent Publication Hei 1-254731 discloses that a curing agent prepared by heating and reacting N,N-dialkylaminoalkylamine, an amine having two amino groups and urea is effective as a latent type curing agent.
- the synthesis of this curing agent is based on a reaction wherein ammonia is removed from the amino-containing substance and urea.
- ammonia is removed from the amino-containing substance and urea.
- the epoxide which is one of the essential components of the present invention has more than one, preferably more than 1.5 epoxy groups per a molecule and includes, for example, glycidyl ethers obtained by reacting epichlorohydrin with a polyhydric phenol such as bisphenol A, bisphenol F, bisphenol S, hexahydrobisphenol A, tetramethylbisphenol A, catechol, resorcinol, cresol, novolak, tetrabromobisphenol A, trihydroxybiphenyl, benzophenone, bis-resorcinol, bisphenol hexafluoroacetone, hydroquinone, tetramethylbisphenol A, tetramethylbisphenol F, triphenylmethane, tetraphenylethane and bixylenol; polyglycidyl ethers obtained by reacting epichlorohydrin with an aliphatic polyhydric alcohol such as glycerin, neopentyl
- the curing agent may be obtained by reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, and (c) at least one diisocyanate, or (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (d) at least one epoxide having one or more epoxy groups in a molecule, and (c) at least one diisocyanate.
- N,N-dialkylaminoalkylamine used herein is represented by the general formula ##STR3## wherein R is alkyl of 1 to 4 carbon atoms and n is 2 or 3.
- dimethylaminopropylamine diethylaminopropylamine, dipropylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, dipropylaminoethylamine, dibutylaminoethylamine, and the like.
- dimethylaminopropylamine and diethylaminopropylamine are preferred,
- polyamines and monoamines such as metaxylylenediamine, 1,3-bis-(aminomethyl)cyclohexane, isophoronediamine, diaminocyclohexane, phenylenediamine, tolylenediamine, diaminodiphenylmethane, diaminodiphenyl sulfone, piperadine, N-aminoethylpiperadine, benzylamine, cyclohexylamine, and the like.
- polyamines and monoamines such as metaxylylenediamine, 1,3-bis-(aminomethyl)cyclohexane, isophoronediamine, diaminocyclohexane, phenylenediamine, tolylenediamine, diaminodiphenylmethane, diaminodiphenyl sulfone, piperadine, N-aminoethylpiperadine, benzylamine, cyclo
- amines metaxylylenediamine, 1,3-bis(aminomethyl)cyclohexane, isophoronediamine, N-aminoethylpiperadine, cyclohexylamine and benzylamine are particularly preferred.
- the polyamines act as a molecular chain extender and the monoamines act as a molecular weight regulator for a curing agent molecule.
- diisocyanate there may be mentioned isophorone diisocyanate, methaxylylene diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,5-naphthylene diisocyanate, 1,4-phenylene diisocyanate, diphenylmethane-4,4'-diisocyanate, 2,2'-dimethyldiphenylmethane-4,4'-diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and the like, of which diisocyanates having a ring structure are particularly preferred.
- the above-mentioned epoxides namely, one of the essential components of the present invention may be used.
- bisphenol A type epoxide having an epoxy equivalent weight of about 190 bisphenol F type epoxide having an epoxy equivalent weight of about 175, glycidylaniline, and glycidylorthotoluidine, as well as monoepoxides such as phenylglycidylether, methylphenylglycidylether and butylphenylglycidylethe are particularly preferred.
- diepoxides act as a molecular chain extending material and monoepoxides act as a molecular weight adjusting material for a curing agent molecule.
- curing agent (B) prepared by reacting at least one N,N-dialkylaminoalkylamine(a), at least one amine(b) having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, and at least one diisocyanate(c), the molar ratio of (b) to a mole of (a) is 0.02 mole ⁇ (b) ⁇ 3.0 moles, and when the amount of (b) is smaller than 0.02 mole, the product has a low melting point and poor storage stability, whereas when the amount of (b) is greater than 3.0 moles, the product has poor curing property at low temperature.
- the ratio of (c) is such that the chemical equivalent of diisocyanate in (c) per one nitrogen atoms with active hydrogen in (a) and (b) is in the range of 1 chemical equivalent ⁇ diisocyanate ⁇ 1.2 chemical equivalents.
- the chemical equivalent of diisocyanate in the used amount is smaller than 1 chemical equivalent, the product is tacky solid which can hardly be crushed and the epoxide composition has poor storage stability.
- the chemical equivalent of diisocyanate in the used amount is greater than 1.2 chemical equivalents, the product has a high melting point and poor low temperature curing properties.
- curing agent (C) prepared by reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (c) at least one diisocyanate, and (d) at least one epoxide having one or more epoxy groups in a molecule, the molar ratio of (b) to a mole of (a) is 0.5 mole ⁇ (b) ⁇ 5.0 moles.
- amount of (b) is smaller than 0.5 mole, the product has a low melting point and poor storage stability.
- the amount of (b) is greater than 5.0 moles, the product has poor curing property at low temperature.
- the ratio of (d) is such that the chemical equivalent of epoxide in (d) per one nitrogen atom with active hydrogen in (a) and (b) is in the range of 0.3 chemical equivalent ⁇ epoxide ⁇ 0.9 chemical equivalent.
- the chemical equivalent of epoxide is smaller than 0.3 chemical equivalent or greater than 0.9 chemical equivalent, both low temperature curing properties and storage stability of the product are poor.
- the sum of the chemical equivalent of diisocyanate in (c) and the chemical equivalent of epoxide in (d) per one nitrogen atom with active hydrogen in (a) and (b) is in the range of 1.0 chemical equivalent ⁇ sum of chemical equivalent of diisocyanate and epoxide ⁇ 1.8 chemical equivalents.
- the sum is smaller than 1.0 chemical equivalent, the product has tackiness and poor storage stability, and when the sum is greater than 1.8 chemical equivalents, molecular weight of the product is increased and gelation occurs.
- the composition of the present invention can be obtained by mixing and dispersing powder of the curing agent with the epoxide.
- the epoxide is a liquid, it is preferred to blend a curing agent therewith in predetermined ratio and further mix and disperse it sufficiently by using a device like a mortar.
- the epoxide is a solid, it is preferred to use preliminarily finely crushed epoxide and mix it sufficiently with a curing agent.
- additives may optionally be added as necessary to the one-pack type heat curing epoxide composition of the present invention.
- inorganic powdery materials such as alumina, silica, silica powder, talc, bentonite, calcium carbonate, and cement; asbestos, glass fibers, synthetic fibers, mica, metal powder, as well as thixotropic agent or similar materials.
- other diluent and flame retardants may be added.
- ARALDITE GY-260 together with AEROSIL 300 (a product of Nippon Aerosil K.K.; a particulate silica)
- a sample of about 0.1 to 0.2 g was placed on a hot plate which was set to predetermined temperature, and the time until gelation of the sample was determined.
- a sample was placed in a thermostatic chamber at 45° C. and days until fluidity loss of the sample were recorded.
- the present invention provides an epoxide composition which utilizes a curing agent free from volatile by-product generation during its synthesis, has excellent storage stability, and can be cured rapidly at a relatively low temperature region when heated.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2-97781 | 1990-04-16 | ||
JP2097781A JPH066621B2 (ja) | 1990-04-16 | 1990-04-16 | 一成分系加熱硬化性エポキシド組成物 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5200494A true US5200494A (en) | 1993-04-06 |
Family
ID=14201371
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/683,047 Expired - Lifetime US5200494A (en) | 1990-04-16 | 1991-04-10 | One-pack type epoxide composition |
Country Status (3)
Country | Link |
---|---|
US (1) | US5200494A (ja) |
EP (1) | EP0452866B1 (ja) |
JP (1) | JPH066621B2 (ja) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5444127A (en) * | 1992-10-19 | 1995-08-22 | Henkel Corporation | Tertiary amine derivatives as components of polymer forming systems |
US5543486A (en) * | 1994-01-07 | 1996-08-06 | Ajinomoto Co., Inc. | Epoxy-resin composition containing titanium and/or zirconium alkoxide and latent hardener |
US6486256B1 (en) | 1998-10-13 | 2002-11-26 | 3M Innovative Properties Company | Composition of epoxy resin, chain extender and polymeric toughener with separate base catalyst |
US20030149194A1 (en) * | 2000-01-31 | 2003-08-07 | Sim Chow | Epoxy resin composition |
US20080033116A1 (en) * | 2006-08-02 | 2008-02-07 | Fuji Kasei Kogyo, Co., Ltd. | One-Component Heat Curable Epoxide Composition |
US20100255313A1 (en) * | 2008-03-07 | 2010-10-07 | Omron Corporation | One-pack type epoxy resin composition and use thereof |
EP2426159A1 (en) | 2010-09-01 | 2012-03-07 | Air Products and Chemicals, Inc. | Low temperature curable epoxy compositions |
US20130022818A1 (en) * | 2010-01-29 | 2013-01-24 | Omron Corporation | One-pack epoxy resin composition, and use thereof |
US9505177B2 (en) | 2010-12-02 | 2016-11-29 | Toray Industries, Inc. | Method for producing a metal composite |
US11084960B2 (en) | 2018-05-17 | 2021-08-10 | T&K Toka Co., Ltd. | Curable epoxide composition |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5569733A (en) * | 1994-03-31 | 1996-10-29 | Ppg Industries, Inc. | Tertiary aminourea compositions and their use as catalysts in curable compositions |
JP3364314B2 (ja) * | 1994-03-31 | 2003-01-08 | サンスター技研株式会社 | 加熱硬化性ウレタン組成物 |
KR100691085B1 (ko) * | 2000-12-16 | 2007-03-09 | 가부시키가이샤 아데카 | 경화제 조성물 및 경화성 에폭시 수지 조성물 |
US6451931B1 (en) | 2000-12-29 | 2002-09-17 | Asahi Denki Kogyo Kabushiki Kaisha | Reaction product of primary and tertiary amine-containing compound, dihydrazide an polyisocyanate |
DE60107644T2 (de) * | 2001-01-09 | 2005-12-01 | Asahi Denka Kogyo K.K. | Härterzusammensetzung und härtbare Epoxyharzzusammensetzung |
JP4752131B2 (ja) * | 2001-05-16 | 2011-08-17 | 味の素株式会社 | エポキシ樹脂用潜在性硬化剤及び硬化性エポキシ樹脂組成物 |
US7091286B2 (en) * | 2002-05-31 | 2006-08-15 | Ppg Industries Ohio, Inc. | Low-cure powder coatings and methods for using the same |
WO2005082982A1 (ja) | 2004-02-27 | 2005-09-09 | Toray Industries, Inc. | 炭素繊維強化複合材料用エポキシ樹脂組成物、プリプレグ、一体化成形品、繊維強化複合材料板、および電気・電子機器用筐体 |
JP2007186547A (ja) * | 2006-01-11 | 2007-07-26 | Adeka Corp | エポキシ樹脂用硬化剤組成物および一成分系加熱硬化性エポキシ樹脂組成物 |
US7928170B2 (en) * | 2007-06-22 | 2011-04-19 | Adeka Corporation | Cyanate ester, epoxy resin and curing agent of phenol resin and epoxy compound-modified polyamine |
US7910667B1 (en) * | 2009-09-11 | 2011-03-22 | Air Products And Chemicals, Inc. | Low temperature curable epoxy compositions containing phenolic-blocked urea curatives |
WO2015104278A1 (de) * | 2014-01-10 | 2015-07-16 | Basf Se | Epoxidharzsysteme mit piperidinderivaten als härter |
JP6331526B2 (ja) | 2014-03-14 | 2018-05-30 | オムロン株式会社 | 樹脂組成物およびその硬化物 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5114999A (en) * | 1974-06-21 | 1976-02-05 | Veba Chemie Ag | Seikeitai oyobi hifukubutsunoseizohoho narabini soreraoseizosurutamenoseikeiyososeibutsu |
US4036795A (en) * | 1974-09-20 | 1977-07-19 | Kansai Paint Co., Ltd. | Aqueous cationic coating from amine-epoxy adduct, polyamide, and semiblocked polyisocyanate, acid salt |
US4480082A (en) * | 1982-08-12 | 1984-10-30 | Canadian Patents & Development Limited | Epoxy resin fortifiers based on aromatic amides |
JPS61155420A (ja) * | 1984-12-22 | 1986-07-15 | チバ‐ガイギー アクチエンゲゼルシヤフト | 熱硬化性エポキシ樹脂組成物及びこれより熱硬化によつて得られる生成物 |
JPS62146915A (ja) * | 1985-12-20 | 1987-06-30 | Asahi Denka Kogyo Kk | 硬化性エポキシ樹脂組成物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1122254B (de) * | 1960-07-05 | 1962-01-18 | Bayer Ag | Verfahren zur Herstellung von primaere Amino- und Harnstoffgruppen aufweisenden hoehermolekularen Verbindungen |
CH515952A (de) * | 1968-05-27 | 1971-11-30 | Reichhold Albert Chemie Ag | Verfahren zum Härten von Expoxydharzen |
AT392284B (de) * | 1987-09-03 | 1991-02-25 | Vianova Kunstharz Ag | Verfahren zur herstellung kationischer lackbindemittel und deren verwendung |
-
1990
- 1990-04-16 JP JP2097781A patent/JPH066621B2/ja not_active Expired - Lifetime
-
1991
- 1991-04-10 US US07/683,047 patent/US5200494A/en not_active Expired - Lifetime
- 1991-04-15 EP EP91106022A patent/EP0452866B1/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5114999A (en) * | 1974-06-21 | 1976-02-05 | Veba Chemie Ag | Seikeitai oyobi hifukubutsunoseizohoho narabini soreraoseizosurutamenoseikeiyososeibutsu |
US4036795A (en) * | 1974-09-20 | 1977-07-19 | Kansai Paint Co., Ltd. | Aqueous cationic coating from amine-epoxy adduct, polyamide, and semiblocked polyisocyanate, acid salt |
US4480082A (en) * | 1982-08-12 | 1984-10-30 | Canadian Patents & Development Limited | Epoxy resin fortifiers based on aromatic amides |
JPS61155420A (ja) * | 1984-12-22 | 1986-07-15 | チバ‐ガイギー アクチエンゲゼルシヤフト | 熱硬化性エポキシ樹脂組成物及びこれより熱硬化によつて得られる生成物 |
JPS62146915A (ja) * | 1985-12-20 | 1987-06-30 | Asahi Denka Kogyo Kk | 硬化性エポキシ樹脂組成物 |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5444127A (en) * | 1992-10-19 | 1995-08-22 | Henkel Corporation | Tertiary amine derivatives as components of polymer forming systems |
US5543486A (en) * | 1994-01-07 | 1996-08-06 | Ajinomoto Co., Inc. | Epoxy-resin composition containing titanium and/or zirconium alkoxide and latent hardener |
US6486256B1 (en) | 1998-10-13 | 2002-11-26 | 3M Innovative Properties Company | Composition of epoxy resin, chain extender and polymeric toughener with separate base catalyst |
US20030144416A1 (en) * | 1998-10-13 | 2003-07-31 | 3M Innovative Properties Company | High strength epoxy adhesive and uses thereof |
US6800157B2 (en) | 1998-10-13 | 2004-10-05 | 3M Innovative Properties Company | Bonding members with epoxy composition containing chain extender, toughener and catalyst |
US7507778B2 (en) | 2000-01-31 | 2009-03-24 | Huntsman Advanced Materials Americas Inc. | Polyepoxide, (cyclo)aliphatic polyamine and solid polyisocyanate |
US20030149194A1 (en) * | 2000-01-31 | 2003-08-07 | Sim Chow | Epoxy resin composition |
US20060247333A1 (en) * | 2000-01-31 | 2006-11-02 | Huntsman Advanced Materials Americas Inc. | Epoxy resin composition |
US7141629B2 (en) * | 2000-01-31 | 2006-11-28 | Huntsman Advanced Materials Americas Inc. | Epoxy resin composition |
US20080033116A1 (en) * | 2006-08-02 | 2008-02-07 | Fuji Kasei Kogyo, Co., Ltd. | One-Component Heat Curable Epoxide Composition |
US7479527B2 (en) | 2006-08-02 | 2009-01-20 | Fuji Kasei Kogyo Co., Ltd. | Polyepoxide and reaction product of aminoalkylimidazole, polyamine, urea and diepoxide as curing component |
US20100255313A1 (en) * | 2008-03-07 | 2010-10-07 | Omron Corporation | One-pack type epoxy resin composition and use thereof |
US20130022818A1 (en) * | 2010-01-29 | 2013-01-24 | Omron Corporation | One-pack epoxy resin composition, and use thereof |
EP2426159A1 (en) | 2010-09-01 | 2012-03-07 | Air Products and Chemicals, Inc. | Low temperature curable epoxy compositions |
US9279032B2 (en) | 2010-09-01 | 2016-03-08 | Air Products And Chemicals, Inc. | Low temperature curable epoxy compositions |
US9505177B2 (en) | 2010-12-02 | 2016-11-29 | Toray Industries, Inc. | Method for producing a metal composite |
US11084960B2 (en) | 2018-05-17 | 2021-08-10 | T&K Toka Co., Ltd. | Curable epoxide composition |
Also Published As
Publication number | Publication date |
---|---|
JPH066621B2 (ja) | 1994-01-26 |
EP0452866A2 (en) | 1991-10-23 |
JPH03296525A (ja) | 1991-12-27 |
EP0452866A3 (en) | 1992-11-25 |
EP0452866B1 (en) | 2003-03-12 |
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